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6-hydroxymelatonin

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EntityQ20707319· pop 6· linked from 642 articles

6-hydroxymelatonin

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Also known as 6-OH-melatonin, 6-OH-MLT, Lopac-H-0627

6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin. 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through hydroxylation. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.

Chemical data

Formula
C13H16N2O3
Molecular weight
248.28 g/mol
IUPAC name
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
SMILES
CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
InChIKey
OMYMRCXOJJZYKE-UHFFFAOYSA-N
XLogP
1.2
Polar surface area
74.4 Ų
H-bond donors
3
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
248.116092
Show 3 more facts
chemical formula
C₁₃H₁₆N₂O₃
canonical SMILES
CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
subject has role
cardiotonic
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

3 sections
Contents
  • Role in metabolism
  • See also
  • References

6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin. 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through hydroxylation. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.

== Role in metabolism == The determination of 6-OHM in human urine has been used to track the metabolism and excretion of melatonin using LC-MS/MS, providing quantifiable insights into circadian rhythm regulation and its oxidative role as a biomarker. 6-OHM is one of four of the primary metabolic products of melatonin in the liver and is also a byproduct of its breakdown due to exposure to light. It is known to be very effective in protecting cells from oxidative damage caused by ultraviolet (UV) radiation. Based on comparisons with other melatonin-related compounds, it is suggested that the protective effects of 6-OHM in mitigating oxidative stress are primarily attributed to their ability to scavenge free radicals.

Excerpted from Wikipedia’s “6-hydroxymelatonin” article, available under the CC BY-SA 4.0 licence.

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